PERGAMON Organic Geochemistry 30 (1999) 119132

Waxes and asphaltenes in crude oils

Nguyen X. Thanh a, M. Hsieh b, R.P. Philp b, *
a
Department of Geochemistry, Branch of Vietnam Petroleum Institute, R.020 Block G1, Thanh Da hotel, Binh Thanh District, Ho Chi
Minh City, Vietnam
b
School of Geology and Geophysics, University of Oklahoma, Norman, OK 73019, USA
Received 28 March 1998; accepted 3 November 1998
(returned to author for revision 26 August 1998)

Abstract

High molecular weight (HMW) hydrocarbons (>C40) and asphaltenes are important constituents of petroleum
and can cause problems related to crystallization and deposition of paran waxes during production and
transportation as well as in the formation of tar mats. However, traditional methods to isolate asphaltene fractions,
by adding 40 volumes in excess of low boiling point solvents such as pentane, hexane or heptane, can produce
asphaltene fractions which are contaminated with a signicant amount of microcrystalline waxes (>C40). The
presence of these microcrystalline waxes in the asphaltene fractions has the potential to provide misleading and
ambiguous results in modeling and treatment programs. The sub-surface phase behaviour of an asphaltene fraction
will be quite dierent from that of a wax-contaminated asphaltene fraction. Similarly accurate modelling of wax
drop-out requires information on pure wax fractions and not asphaltene-dominated fractions. Hence the goal of this
paper is to describe a novel method for the preparation of wax-free asphaltene fractions. In addition, this method
provides a quantitative subdivision of the wax fraction into pentane soluble and insoluble waxes which, when
correlated with physical properties of crude oil such as viscosity, pour point, cloud point, etc., may help explain
causes of wax deposition during production, transportation and storage of petroleum. # 1999 Elsevier Science Ltd.
All rights reserved.

Keywords: Waxes; asphaltenes; crude oils; high temperature gas chromatography; depositional environments; high molecular weight
hydrocarbons

1. Introduction oils will be determined primarily by source materials,

The development of high temperature gas chroma-
tography (HTGC) in recent years has permitted geo-
chemists to enter the realm of high molecular weight
hydrocarbons (HMWHC) in the range C40C120 in
crude oils and, to a lesser extent, source rock extracts
(Lipsky and Duy, 1986a,b; Philp, 1994; Heath et al.,
1997; Mueller and Philp, 1998). In most crude oils
these compounds typically extend to about C70. A few
oils have been shown to contain compounds in the
C70C120 range. The distribution of HMWHC in crude
* Corresponding author. E-mail: pphilp@ou.edu
with factors such as migration distances, pressure and
temperature gradients between reservoir and well-head
also playing an important role. Hydrocarbons with
more than 20 carbon atoms are solid at room tempera-
ture and thus crude oils containing large amounts of
hydrocarbons above C20, and more importantly above
C40, have the potential to give rise to serious wax de-
position problems during production, and in some
cases within the reservoir itself (Trindade et al., 1996).
Previous studies have shown that oils with wax con-
tents of at least 2% have the potential for wax depo-
sition problems (Holder and Winkler, 1965; Tuttle,
1983: Ajienka and Ikoku, 1990). Waxes may be preci-
pitated in the production tubing or anywhere along the
pipelines and production facilities until the oils reach

0146-6380/99/$ - see front matter # 1999 Elsevier Science Ltd. All rights reserved.
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120 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132

Fig. 1. Proposed scheme for the qualitative and quantitative separation of asphaltenes, micro- and macrocrystalline waxes. The
numbers of each important step are given and these are referred to in the text.

the storage tanks. Even in storage tanks, wax depo-
sition may be a problem and co-mingling of two or
more oils, neither of which have paran problems
when produced separately, may lead to the precipi-
tation of waxes. Blending experiments by Escobedo
and Mansoori (1992) have demonstrated that when
oils which separately contain little or no paran wax
are mixed, the blended oil has a higher wax content
than either of the original oils and the asphaltene par-
ticles tend to occulate. Movement and shearing may
prevent deposition in the pipeline but the wax crystals
formed will readily be deposited in the storage tank.
Although the terms micro and macro-crystalline waxes
have been used for many years to dierentiate wax-
types on the basis of their carbon number distributions
and other properties, detailed molecular characteriz-
ation of waxes was rarely undertaken in the past due
to the lack of suitable analytical techniques.
The introduction of HTGC has changed that situ-
ation and now it is possible to qualitatively and quan-
titatively characterize these HMWHC in great detail.
A number of papers have already been published on
this topic including those by Del Rio and Philp
(1992a,b), Carlson et al. (1993) and Wavrek and
Dahdah (1995). These papers generally have been con-
cerned with the characterization of waxes isolated
from crude oils and pipelines and discuss the potential
use of this type of information. In many cases, how-
ever, the concentration of these HMWHCs may be
relatively low and hence techniques may be required to
enhance the concentration of these compounds. Philp
and Bishop (1995); Philp et al. (1995) described one
such concentration technique. Another standardized
method involving acetone precipitation was published
several years ago (Burger et al., 1981).
One of the major problems associated with this
approach is the separation of waxes from non-hydro-
carbons dominated by resin and asphaltene fractions.
Precipitation of asphaltenes with n-pentane will, in
many cases, produce a fraction containing a high con-
centration of microcrystalline waxes (>C40), whose
presence can lead to misinterpretation of geochemical
characteristics of the asphaltene fraction and total wax
composition. The solubility of n-C50 in pentane for
example, is 1.3 mg/100 ml, and hence it is not
altogether surprising that microcrystalline waxes and
 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132 121

Fig. 2. (a) HTGC chromatogram of a crude oil from the Uinta Basin. GC conditions are described in the text. This oil had lost the
light ends through evaporation. (b) HTGC chromatogram of the asphaltene precipitate isolated from the crude oil used for (a) and
isolated by the classical pentane precipitation method. (c) HTGC chromatogram of the asphaltene fraction isolated from the same
oil using the procedure described in this paper. Note the complete absence of any wax components in this sample, illustrating the
quantitative separation of the wax from the asphaltene.

asphaltenes will coprecipitate. On the other hand the
solubility of macrocrystalline waxes (<C40) is 4.86 g/
100 ml. Hence the microcrystalline waxes tend to exist
as very ne solid particles suspended in an oil and will
tend to occulate and precipitate out under appropri-
ate conditions. Once precipitation or deposition of
these waxes occurs, precipitation and deposition of
compounds with lower carbon numbers will tend to
precipitate as well. Despite the fact that microcrystal-
line waxes (>C40) are often present in relatively low
concentrations in most oils it is this fraction of the oil
which can cause the most problems in terms of pro-
duction. Thus it is essential that a method be available
for the accurate assessment of this fraction in the oil
as well as an accurate assessment of the associated as-
phaltene fraction. Any program modeling phase beha-
viour of waxes or asphaltenes needs an accurate
indication of the wax and asphaltene content of the
oil. Misleading and ambiguous results will be obtained
if either fraction is cross-contaminated.
In addition to the problems associated with the
modeling mentioned above it is also desirable to isolate
pure wax and asphaltene fractions for a variety of
other purposes. For example, if one wanted to predict
the occurrence of wax problems in a specic area, one
must relate the abundance of waxes in known pro-
duction for a particular petroleum system. One
extreme example might be the situation where two
active source rocks might be generating a wax rich oil
and an asphaltene rich oil, respectively. If oils from
these two sources were to mix it would then be import-
ant to have a clear idea of the wax and asphaltene con-
tent of each sample in order to accurately predict the
expected composition of the mixed oil.
One nal reason for this type of information is re-
lated to treatment of wax and asphaltene problems.
An accurate assessment of any deposit or precipitate in
122 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132

Fig. 3. (a) HTGC chromatogram of the total wax fraction isolated using the procedure described in this paper. This corresponds to
the total wax isolated at step 3 of the procedure shown in Fig. 1. (b) and (c), respectively, show the chromatograms for the macro-
and micro-crystalline waxes recovered from steps 5 and 6 shown in Fig. 1.

production is essential for developing an ecient
clean-up procedure. A wax build up may be prevented
or minimized by the addition of light hydrocarbons.
However if the build-up resulted predominantly from
the addition of asphaltenes, then addition of light
hydrocarbons would exacerbate the situation, leading
to the build-up of additional asphaltene deposits. To
address problems regarding heavy organic deposits
(HMWHC), it is necessary to characterize, in detail,
these components in crude oils. This will require accu-
rate separations and quantitation of asphaltenes, paraf-
n waxes, and resins. Based on these properties it may
be possible to develop relationships among these frac-
tions.
In this paper, we will describe a method to separate
waxes from asphaltenes quantitatively and qualitat-
ively. The method will be illustrated with results
obtained from its application to oils from a variety of
sources. Previous attempts to characterize asphaltenes
by pyrolysisGC and to use the resulting chromato-
grams to correlate degraded and non-degraded oils
(Behar and Pelet, 1985) can be severely aected by the
presence of waxes in the asphaltene fractions. Results
will also be presented to demonstrate how these data
can also be used to dierentiate oils from various
depositional environments. One nal and very critical
observation is the fact that waxy oils are not necess-
arily limited to those sourced from higher plant ma-
terial, as previously suggested by Hedberg (1968).
Many oils from lacustrine and marine sources also
contain signicant concentrations of HMWHC with
more than 40 carbon atoms.
2. Experimental
The initial step in this method involves adsorption
of the oil on alumina (1, these numbers refer to the
steps numbered in Fig. 1), using approximately 1 g of
oil dissolved in 10 ml of hot p-xylene (at least 808C) to
ensure complete dissolution of any wax crystals.
Following adsorption, the alumina is extracted with p-
xylene for 48 h (2), although this time period can be
signicantly reduced if the microcrystalline wax con-
tent (>C40) of the oil is low. Following the extraction,
the p-xylene extract is concentrated and the wax preci-
pitated with acetone at 218C (3, Burger et al., 1981).
Cold pentane (218C) is added to the precipitate to a
 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132 123

Fig. 4. (a) HTGC of an asphaltene fraction isolated by the classical pentane procedure, again showing a high wax component that
precipitated along with the asphaltenes. (b) HTGC chromatogram of the wax free asphaltene isolated from the same oil using the
method described in Fig. 1. (c) PyGC chromatogram obtained from the pyrolysis of the asphaltene fraction shown in (a). Note
the relatively high concentration of hydrocarbons in the C30 range resulting from incomplete separation of n-alkanes from the as-
phaltene fraction. (d) PyGC chromatogram obtained from the pyrolysis of the asphaltene fraction shown in (b). Note the absence
of any enhanced concentration of hydrocarbons due to the pure nature of the asphaltene fraction.

concentration of about 2 mg/ml and the solution
allowed to stand overnight (4). Following stirring and
centrifugation with cold n-pentane, two fractions are
obtained with the macrocrystalline waxes being in sol-
ution (5) and microcrystalline waxes with predomi-
nance of HMWHCs beyond C40 being present as
precipitate (6). The material that remains adsorbed to
the alumina after the initial extraction step is initially
washed with pentane to remove any residual p-xylene,
and subsequently extracted with a mixture of chloro-
form/methanol (95:5) for at least 6 h (7). This pro-
cedure will eectively extract the adsorbed asphaltenes
and resins from the alumina. They can subsequently be
separated by pentane precipitation (8).
Hence the end products of this procedure are: (i) a
wax-free asphaltene fraction and (ii) an asphaltene-free
wax concentrate which, if desired, can be subdivided
into micro (5)- and macrocrystalline (6) wax fractions.
2.1. Quantitation and recovery
The recovery eciency (steps 1 and 2, Fig. 1) was
checked by using 200 mg Polywax 655, corresponding
to the macrocrystalline wax content of crude oils.
Results indicate that on average 99.5% of the Polywax
655 was recovered after 48 h of extraction.
In order to check the eciency of the asphaltene
recovery (7), 10 and 20 mg quantities of asphaltene
fractions, devoid of waxes as veried by GC, were
used. The results indicated that the average recovery in
both cases was 99%, using a mixture of chloroform
and methanol (95:5) for 6 h to extract the asphaltenes
from the alumina.
2.2. GC analysis
All GC analyses described in this paper were
performed using a CarloErba GC8000 gas chromato-
graph equipped with an on-column injector and a
25 m0.32 mm i.d., 0.1 mm HT-5 column. Helium was
used as carrier gas and the column was programmed
from 60 to 3808C with a program rate of 48C/min.
Asphaltenes were pyrolysed at a temperature of
8008C for 20 s using the coil probe of the Chemical
Data Systems Pyroprobe 122 system. The pyrolysates
were swept from the heated interface (3008C) under a
stream of helium onto a fused silica DB-5 capillary
column (J&W Scientic, 30 m0.32 mm i.d.) installed
 124
N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132

Fig. 5. Terpane and sterane chromatograms for the two oils used in a comparative study of their wax and asphaltene components. On the basis of these biomarker data and
other parameters it could be concluded that the oils were source related.
 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132 125

Fig. 6. HTGC traces of the two oils used in this study plus the HTGC traces of the wax components isolated from both oils. Note
the similarities in the wax content of the oils plus the similarities in the distribution of the individual compounds in the wax frac-
tion HTGC chromatogram.

in a Varian 3300 gas chromatograph equipped with a
ame ionization detector (FID). The column oven tem-
perature was held at 258C for 4 min and sub-
sequently increased to 3008C at the rate of 48C/min.
3. Results and discussion
A recent paper by Heath et al. (1997) described a
procedure with some similarities to our method, for
the recovery of HMWHC from a series of biodegrada-
tion experiments. It is important to emphasize at the
outset of this discussion that despite some initial simi-
larities, the two methods were developed for dierent
purposes. The work described in this paper is speci-
cally concerned with a method that has the ability to
qualitatively and quantitatively separate waxes from
asphaltenes and also macrocrystalline waxes from
microcrystalline waxes.
The procedure described herein has been designed to
work on samples of approximately 1 g in size, but can
be scaled depending upon the amount of oil available
and how much material is required from the separation
step. Secondly the duration of the extraction steps of
the waxes from the adsorbed material on the alumina
may vary depending upon the nature of the wax. In
our experiments p-xylene extracts were collected every
2 h and characterization of these extracts indicated
that most of macrocrystalline waxes were recovered in
the rst 4 h of extraction. As a result, the time for the
wax extraction with p-xylene is mainly dependent upon
the amount of microcrystalline waxes in the crude oil
and this time can be reduced signicantly if a prelimi-
nary idea of the nature of the waxes (micro versus
macro) is available.
To illustrate the nature of the problem, Fig. 2(a)
shows the high temperature gas chromatogram
(HTGC) of a crude oil with high molecular weight
hydrocarbons extending to at least C65. The asphalt-
enes, obtained by the widely-used pentane precipitation
method, when analysed by HTGC, produced the chro-
matogram shown in Fig. 2(b). A signicant part of the
asphaltene fraction in this case was present as a micro-
crystalline wax (which is a more common occurrence
than has been noted in the past). In most cases as-
phaltenes are not routinely analyzed by HTGC, so the
presence of these waxy components is not observed.
Further purication of the asphaltenes would not
126 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132

Fig. 7. HTGC traces of the asphaltene fractions isolated by the conventional pentane precipitation method plus the pyGC traces
from both of these oils. Note that the pyGC trace of oil A (whose asphaltene fraction included some HMWHC) shows an
enhancement around C30 in the pyrogram as a result of the presence of these components in the asphaltene.

necessarily remove the wax component simply because
of their HMW and extremely poor solubility in sol-
vents such as pentane commonly used to purify the as-
phaltenes (solubility of n-C60 in pentane is 1 mg/100
ml). In Fig. 2(c) the HTGC trace is shown for the as-
phaltene fraction isolated from the same oil using the
procedure shown in Fig. 1. Clearly the asphaltene frac-
tion no longer contains any wax components, indicat-
ing complete separation of waxes from the asphaltene
fraction. The corresponding wax fraction isolated from
this oil using the procedure in Fig. 1 is shown in
Fig. 3(a) and the n-pentane soluble and insoluble
waxes are displayed in Fig. 3(b) and (c). The pentane-
soluble waxes contain predominantly n-alkanes
(<C40C45) and the insoluble waxes contain mainly
microcrystalline waxes (>C40) whose extremely poor
solubility may potentially cause wax deposition pro-
blems, especially in storage tanks. The quantitation of
these higher carbon number components can be corre-
lated with other physical properties such as pour
point, cloud point or viscosity, to help explain causes
of wax deposition problems.
Asphaltene fractions isolated from biodegraded
crude oils may be pyrolysed. The chromatogram of the
pyrolysis products generated in this manner will closely
resemble the pyrolysis products that may be generated
from the corresponding non-degraded oil (Behar and
Pelet, 1985). Typically for these pyrolysis reactions the
asphaltenes are isolated by the standard pentane pre-
cipitation techniques and possibly puried once or
twice. However, rarely if ever are the asphaltene frac-
tions analysed by GC prior to analysis to determine if
they contain any free hydrocarbons. In an earlier study
we demonstrated the presence of HMWHC in asphalt-
ene fractions (Del Rio and Philp, 1992a) and specu-
lated as to whether these compounds were actually
part of the asphaltene structure or simply trapped in
the complex moeity.
In this study we have revisited this problem. In
Fig. 4(a) the asphaltene fraction isolated from a ter-
tiary lacustrine oil by the classical pentane technique
has been analysed by HTGC and the presence of a
wax component is clearly indicated. Fig. 4(b) shows
the HTGC analysis of the asphaltene fraction isolated
using the method described in this paper and clearly
no wax component is present in the asphaltene frac-
tion. Characterization of these two asphaltene fractions
by pyGC produced the chromatograms shown in
Fig. 4(c) and (d), respectively. The dierences between
these two chromatograms is clearly evident, with the
wax component in the classical asphaltene fraction
introducing a signicant hump in the higher molecular
 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132 127

Fig. 8. HTGC chromatograms showing the wax free nature of the asphaltenes isolated using the procedure described in this paper
along with their corresponding pyGC traces. Note that in this case both pyGC chromatograms are virtually identical, illustrating
that these ngerprints provide another useful correlation tool if the asphaltenes are pure in the rst instance.

weight region of the chromatogram around C30 and a
less visible enhancement around C50. If the asphaltene
pyrolysis products had been analysed on a HTGC col-
umn, it can be predicted that another maximum would
have occurred in the C40C50 region of the chromato-
gram. The point of this is to demonstrate that the pre-
sence of the HMWHC in the asphaltene concentrate
will signicantly alter the appearance of the chromato-
gram, which in turn could lead to serious errors in the
interpretation of the data.
In another example two oils shown from biomarker
analysis to be related to each other were treated to iso-
late the wax and asphaltene fractions. On the basis of
sterane and hopane distributions (Fig. 5) it has been
proposed that these oils are source-related, although of
slightly diering maturities. The waxes isolated from
the oils, shown in Fig. 6(b), are predominantly micro-
crystalline and are very similar in composition. The
whole oil GC traces shown on the left hand side of
Fig. 6 indicate that oil A appears to contain a signi-
cantly higher proportion of the HMWHC in the region
above C20, although quantitatively the wax contents of
the two oils are very similar.
One signicant dierence between these oils is their
asphaltene content, 0.47% for oil A and 5.95% for oil
B. Interestingly enough, isolation of the asphaltene
fraction from oil A with subsequent characterization
by HTGC produces the chromatogram shown in
Fig. 7(a). Oil B asphaltene isolated in the traditional
manner does not include any HMWHC that could be
characterized by HTGC. Characterization of both as-
phaltenes by HTGC shows the enhancement again of
the chromatogram for oil A in the region around C30
resulting from this `contamination' of the asphaltene
fraction. (Note that the pyGC experiments were per-
formed by conventional GC and so the HMW com-
ponents will not be observed in the fractions.) Finally,
the chromatograms shown in Fig. 8 were obtained
from these two oils. The HTGC traces for the two as-
phaltenes shown on the left indicate isolation of a pure
asphaltene fraction in each case. The chromatograms
resulting from the pyGC characterization are shown
on the right, and the strong similarities between these
two pyrograms is apparent. The reason for emphasiz-
ing the similarities between these two chromatograms
in Fig. 8 is again to reinforce the notion that the pyrol-
ysis chromatograms of asphaltene products can be
128 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132

Fig. 9. A comparison of the distributions of the branched and cyclic hydrocarbons in oils from dierent types of depositional en-
vironments showing the changes in the distributions as a results of the diering conditions in the depositional environments. (a)
freshwater lacustrine; (b) marine; (c) expanded C40+ region of the chromatogram for the freshwater lacustrine sample; (d)
expanded C40+ region of the chromatogram for the marine sample.
N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132 129
130 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132
 N.X. Thanh et al. / Organic Geochemistry 30 (1999) 119132
used as an additional correlation tool for crude oils if
pure asphaltene fractions that contain no wax com-
ponent are used for this purpose. Lack of correlation
between asphaltene fractions in the previous studies
may have been related to the purity of asphaltene frac-
tions being used.
As part of a separate survey, we have been applying
this method to a collection of oils from dierent basins
worldwide. Whilst the results of that study will be
described elsewhere, Fig. 9 shows the HTGC chroma-
tograms for an oil derived from a marine source rock
compared to that from a lacustrine source rock. The
rst point to note here is the carbon number range of
the HMWHC, illustrating the abundance of these com-
pounds in oils from all types of source materials.
Secondly variations in the distributions of the
branched and alkylcyclohexane type compounds are
marked on these chromatograms. In extending the
original work of Carlson et al. (1993), it can be shown
that variations in the distributions of these compounds
provide a very powerful method for distinguishing oils
from marine versus lacustrine source rocks.
Furthermore salinity dierences from within these en-
vironments can also be distinguished. In summary a
marine pattern features an odd/even predominance a
lacustrine pattern an even/odd predominance, a fresh/
brackish lacustrine pattern a weak even/odd or no pre-
dominance, and an evaporitic marine/evaporitic lacus-
trine pattern a marked even/odd predominance.
4. Summary and conclusions
This paper has described a novel method for the iso-
lation of wax-free asphaltene fractions and asphaltene-
free wax fractions. Furthermore it also provides a
method to subdivide the wax fraction into micro- and
macrocrystalline fractions, which might help us to
explain causes of wax deposition problems. In our
opinion this is a very important method because deter-
mination of asphaltene and wax contents of crude oils
can play a very important role in eliminating, or at
least alleviating, production problems associated with
wax and asphaltene deposition. A more accurate
assessment of the composition of the deposits at well-
heads and in pipelines will also provide better infor-
mation when protocols are developed to remediate
such problems. In the past, incorrect characterization
of these fractions has led to potentially serious errors
in the way problems are treated. Furthermore the ap-
plication of this method to other problems (such as tar
mats, for example) may lead to a better understanding
of the way in which these materials are formed.
Isolation of an asphaltene fraction by pentane precipi-
tation alone may not tell a complete story, because the
asphaltene fraction isolated in this way can also con-
131
tain a signicant proportion of waxes. The ability to
isolate pure asphaltene fractions will also enhance our
ability to use the pyrolysis products from these frac-
tions for crude oil correlations. Finally, the use of this
approach produces pure wax fractions which can be
analysed by HTGC. The resulting high resolution
chromatograms provide a ngerprint which can be
used to dierentiate oils derived from dierent source
materials deposited in dierent environments.
Associate EditorJ. Collister
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